Roderick Blank (Simon Baker) is a successful young businessman with a great job as an executive for "Swallows", a high end fast food restaurant chain, and a beautiful fiancée, Fiona Wormwood (Julie Bowen). On the day of his bachelor party, he is e-mailed a list of all the women he has slept with. Strangely, while the list has 101 names, his fiancée is only number 29. He assumes the list is a prank, courtesy of his best friends Zack (Neil Flynn) and Lester (Dash Mihok)—until he meets number 30, Carlotta Valdez, who is the stripper at his bachelor party. After sleeping with Carlotta, he realizes the list does, in fact, comprise all of his sexual partners, both past and future.